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Compounds with physiological cooling effect

Inactive Publication Date: 2006-04-18
QAROMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0012]The present invention provides a novel series of derivatives of 2,3-dimethyl-2-isopropylbutyric acid, with pronounced physiologic

Problems solved by technology

Disadvantages of menthol include its strong “stinging” smell, bitter taste, burning sensation in high concentration and high volatility.
These undesirable properties limit applications of menthol to some extent.

Method used

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  • Compounds with physiological cooling effect
  • Compounds with physiological cooling effect
  • Compounds with physiological cooling effect

Examples

Experimental program
Comparison scheme
Effect test

example 1 preparation

of N-(2-hydroxyethyl)-2,3-dimethyl-2-isopropylbutyramide (1)

[0019]A mixture of 19.5 g 2-aminoethanol and 50 mL anhydrous hexanes was cooled to 0° C. Under mechanical stirring 20 g freshly distilled 2,3-dimethyl-2-isopropylbutyryl chloride was added dropwise over a period of one hour while maintaining the reaction temperature below 5° C. The reaction mixture was then stirred for one more hour at this temperature followed by one hour at room temperature.

[0020]50 mL water was added and the top organic layer was separated and washed with water till is neutral. The solvent was evaporated and 21.5 g crude product (99+% GC purity) was obtained. The product was recrystallized from acetone / water.

example 2 preparation

of N-(3-hydroxypropyl)-2,3-dimethyl-2-isopropylbutyramide (4)

[0021]The procedure of Example 1 was repeated using 3-aminopropyl in place of 2-aminoethanol. N-(3-hydroxypropyl)-2,3-diemthyl-2-isopropylbutyramide (4, 99+% GC purity) was obtained as very viscous oil.

example 3 preparation

of N-(2-methoxyethyl)-2,3-dimethyl-2-isopropylbutyramide (2)

[0022]A mixture of 7.74 g 2-methoxyethylamine, 10.95 g triethylamine and 50 mL anhydrous hexanes was cooled to below 5° C. and under mechanical agitation 20 g freshly distilled 2,3-dimethyl-2-isopropylbutyryl chloride was added dropwise over a period of 30 minutes while maintaining the reaction temperature below 25 ° C. After addition the reaction mixture was stirred for 30 minutes at this temperature followed by one hour at room temperature.

[0023]50 mL water was added, the top organic layer was separated and washed with 20 mL 5% NaOH solution followed by water till it was neutral. The solvent was evaporated and 24.2 g crude product (2. 98.5+% GC purity) was obtained as viscous oil.

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Abstract

Novel compounds of 2,3-dimethyl-2-isopropylbutyric acid were claimed in this patent to possess pronounced cooling effect on the skin and on the mucous membranes of the body. These compounds also possess good taste quality and low melting points with no malodor. The preparations and some illustrative application of these compounds are also disclosed.

Description

BACKGROUND OF THE INVENTION[0001]This invention relates to compounds having a physiological cooling effect on the skin and on the mucous membranes of the body, particularly those of the mouth, nose and throat.[0002]Menthol exists abundantly in nature and has been known for a long time as a physiological cooling compound. It is well established that the “cooling” effect of menthol is a physiological effect due to the direct action of menthol on the nerve ends of the human body responsible for the detection of hot or cold and is not due to latent heat of evaporation or dissolution. Menthol has been used widely in cigarettes, cosmetics, toothpastes, chewing gum, sweets, and medicines. Disadvantages of menthol include its strong “stinging” smell, bitter taste, burning sensation in high concentration and high volatility. These undesirable properties limit applications of menthol to some extent.[0003]Since 1960's, researchers have been working on discovering synthetic substitutes of menth...

Claims

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Application Information

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IPC IPC(8): C07C233/05
CPCC07C233/18
Inventor SUN, HONG SUN
Owner QAROMA
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